Dicyclohexylcarbodiimide → HCID 178477928, compound

HRID 1666111Notes

Reaction equation

HRID 1666111 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[CH2:4][OH:5].[C@H:11]1([N:20]=[C:21]=S)[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12]1.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1.C(OCC)(=O)C.O>[Cl:10][C:6]1[C:3]2[CH2:4][O:5][C:21]([NH:20][C@H:11]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[CH2:13][CH2:12]3)=[N:1][C:2]=2[CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 7018249(R)-(-)-1-Indanyl isothiocyanateHCID 21925574(2-Amino-6-chlorophenyl)methanol

Product 1

HCID 178477928HCID 178477928, compoundYield 36%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
23 °C

Procedure

To a stirred solution of commercially available 2-amino-6-chlorobenzyl alcohol (CAS-no. 39885-08-0) (315 mg, 2 mmol) in tetrahydrofuran (4 ml) at 23° C. was added commercially available (R)-(−)-1-indanyl isothiocyanate (CAS-no. 737000-97-4) (324 ul, 2 mmol) and the mixture was stirred at 23° C. for 18 h, then at reflux for another 3 h. Cooled to 23° C., the solvent was removed in vacuum, the residue was dissolved in acetonitrile (4 ml), added dicyclohexylcarbodiimide (DCC) (619 mg, 3.0 mmol) and refluxed for 2 h. Cooled to room temperature, diluted with ethyl acetate and water, added little 1 M NaH2PO4.2H2O solution to achieve pH 4, separated phases, washed organic layer with brine and dried over sodium sulfate. Removal of the solvent in vacuum left a yellow foam, which was purified by silica gel flash chromatography with n-heptane and ethyl acetate to give the title compound as a light yellow oil (215 mg, 36%), MS (ISP) m/e=299.1 [(M+H)+].

Workup

  1. temperatureat reflux for another 3 h
  2. temperatureCooled to 23° C.
  3. customthe solvent was removed in vacuum
  4. dissolutionthe residue was dissolved in acetonitrile (4 ml)
  5. temperaturerefluxed for 2 h
  6. temperatureCooled to room temperature
  7. customseparated phases
  8. washwashed organic layer with brine
  9. dry with materialdried over sodium sulfate
  10. customRemoval of the solvent in vacuum
  11. waitleft a yellow foam, which
  12. customwas purified by silica gel flash chromatography with n-heptane and ethyl acetate

Sources & evidence

ORD record
ord-710910d8543640cc948fa21e170b7426
Source dataset
uspto-grants-2011_10
Patent number
US08044047B2

Reaction notes

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